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  3. (4S,4aS,6S,8aS)-4,6-dihydroxy-2-[(1R,2R,3R)-2-(2-hydroxyethyl)-2-methyl-3-[(E,2R)-5-methylhex-3-en-2-yl]cyclopentyl]-8a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-1-one

SCS-C003438

(4S,4aS,6S,8aS)-4,6-dihydroxy-2-[(1R,2R,3R)-2-(2-hydroxyethyl)-2-methyl-3-[(E,2R)-5-methylhex-3-en-2-yl]cyclopentyl]-8a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-1-one

Pathway: Terpenoids Superclass: Steroids Class: Cholestane steroids
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Chemical Structure

Structure of (4S,4aS,6S,8aS)-4,6-dihydroxy-2-[(1R,2R,3R)-2-(2-hydroxyethyl)-2-methyl-3-[(E,2R)-5-methylhex-3-en-2-yl]cyclopentyl]-8a-methyl-4,4a,5,6,7,8-hexahydronaphthalen-1-one
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3D conformers are computationally generated from SMILES by RDKit for visualization and download; they are not experimental crystal or NMR structures.
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Source Information

Subergorgia suberosa (gorgonian)
Kingdom Metazoa Phylum Cnidaria Class Anthozoa Order Malacalcyonacea Family Subergorgiidae Genus Subergorgia Species Subergorgia suberosa
Sanya Meishan
DOI: 10.1039/c4np00144c  · Natural Product Reports

Drug-likeness (Lipinski Ro5)

Molecular Weight
418.6 Da
Threshold ≤ 500
ALogP
4.29
Threshold ≤ 5
H-Bond Donors
3
Threshold ≤ 5
H-Bond Acceptors
4
Threshold ≤ 10
Passes Lipinski Rule of Five — drug-like candidate

Chemical Properties

Molecular Formula:
C26H42O4
Molecular Weight:
418.6180 Da
SMILES:
CC(C)/C=C/[C@@H](C)[C@H]1CC[C@@H](C2=C[C@H](O)[C@H]3C[C@@H](O)CC[C@]3(C)C2=O)[C@]1(C)CCO
InChIKey:
ACZCILMNXPHLSP-ZJCDCYBCSA-N
InChI:
InChI=1S/C26H42O4/c1-16(2)6-7-17(3)20-8-9-21(25(20,4)12-13-27)19-15-23(29)22-14-18(28)10-11-26(22,5)24(19)30/h6-7,15-18,20-23,27-29H,8-14H2,1-5H3/b7-6+/t17-,18+,20-,21+,22-,23+,25-,26+/m1/s1
Calculated Properties
ALogP:
4.287 lipophilicity
TPSA:
77.76 Ų polar surface area
H-Bond Donors:
3
H-Bond Acceptors:
4
Rotatable Bonds:
6
Ring Count:
3 (0 aromatic)
Chiral Centers:
8
Fsp³:
0.8077 fraction sp³ carbon

Database Information

Compound ID:
SCS-C003438
NPClassifier Pathway:
Terpenoids
NPClassifier Superclass:
Steroids
NPClassifier Class:
Cholestane steroids
Glycoside:
No
NPClassifier Status:
Classified
External Links:
General chemistry
PubChem ChemSpider ChEMBL
Natural product databases
COCONUT NP Atlas CMNPD: CMNPD24140

Biological Activity Data

No bioactivity data available for this compound.

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Structure enlarged